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RU2014142038A - SHORT ANTIMICROBIAL LIPOPEPTIDES - Google Patents

SHORT ANTIMICROBIAL LIPOPEPTIDES Download PDF

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RU2014142038A
RU2014142038A RU2014142038A RU2014142038A RU2014142038A RU 2014142038 A RU2014142038 A RU 2014142038A RU 2014142038 A RU2014142038 A RU 2014142038A RU 2014142038 A RU2014142038 A RU 2014142038A RU 2014142038 A RU2014142038 A RU 2014142038A
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lysine
peptide
composition
proline
microbial infection
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RU2014142038A
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RU2627648C2 (en
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Лицзюань ЧЖАН
Робин КАРМАЙКЛ
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Хеликс Байомедикс, Инк.
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/06—Dipeptides
    • C07K5/06086—Dipeptides with the first amino acid being basic
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/05—Dipeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/04—Peptides having up to 20 amino acids in a fully defined sequence; Derivatives thereof
    • A61K38/06—Tripeptides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K38/00—Medicinal preparations containing peptides
    • A61K38/16—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof
    • A61K38/17—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans
    • A61K38/33—Peptides having more than 20 amino acids; Gastrins; Somatostatins; Melanotropins; Derivatives thereof from animals; from humans derived from pro-opiomelanocortin, pro-enkephalin or pro-dynorphin
    • A61K38/34—Melanocyte stimulating hormone [MSH], e.g. alpha- or beta-melanotropin
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/50—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates
    • A61K47/51—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent
    • A61K47/54—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient the non-active ingredient being chemically bound to the active ingredient, e.g. polymer-drug conjugates the non-active ingredient being a modifying agent the modifying agent being an organic compound
    • A61K47/542—Carboxylic acids, e.g. a fatty acid or an amino acid
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
    • A61K8/64—Proteins; Peptides; Derivatives or degradation products thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P15/00—Drugs for genital or sexual disorders; Contraceptives
    • A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/10—Anti-acne agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/02—Local antiseptics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/10—Antimycotics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P37/00—Drugs for immunological or allergic disorders
    • A61P37/08—Antiallergic agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07K—PEPTIDES
    • C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
    • C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
    • C07K5/08—Tripeptides
    • C07K5/0815—Tripeptides with the first amino acid being basic
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
    • Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
    • Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change

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  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Organic Chemistry (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Engineering & Computer Science (AREA)
  • Proteomics, Peptides & Aminoacids (AREA)
  • Epidemiology (AREA)
  • Immunology (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • General Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Gastroenterology & Hepatology (AREA)
  • Biochemistry (AREA)
  • Molecular Biology (AREA)
  • Genetics & Genomics (AREA)
  • Biophysics (AREA)
  • Endocrinology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Zoology (AREA)
  • Dermatology (AREA)
  • Pulmonology (AREA)
  • Birds (AREA)
  • Reproductive Health (AREA)
  • Gynecology & Obstetrics (AREA)
  • Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
  • Cosmetics (AREA)
  • Peptides Or Proteins (AREA)
  • Medicinal Preparation (AREA)

Abstract

1. Пептид формулы:Cлипид-лизин-пролин-N;Cлипид-лизин-d-пролин-NH;Cлипид-лизин-гистидин-NHилиCлипид-лизин-аргинин-NH.2. Пептид по п. 1, где Cлипид является липидным фрагментом лауриновой кислоты (С12), миристиновой кислоты (С14), пентадекановой кислоты (С15), пальмитиновой кислоты (С16) или стеариновой кислоты (С18).3. Пептид по п. 1, где пептид представляет собойпальмитоил-лизин-пролин-NH;пальмитоил-лизин-d-пролин-NH;пальмитоил-лизин-гистидин-NHилипальмитоил-лизин-аргинин-NH.4. Композиция, содержащая по меньшей мере один пептид по любому из пп. 1-3 и фармацевтически приемлемый носитель.5. Композиция по п. 4, где пептид присутствует в концентрации в диапазоне от примерно 0,1 мкг/мл до примерно 10% (масс./об.).6. Композиция по п. 4 или 5, где композиция представлена в виде аэрозоля, косметического препарата, спрея, эмульсии, жидкости, лосьона, крема, пасты, мази, порошка или пены.7. Композиция по п. 6, которая может быть использована для профилактики или лечения кожных состояний акне, атопического дерматита, розацеа, бактериального вагиноза, перхоти или эпидермофитии стоп.8. Способ профилактики или лечения микробной инфекции кожи или слизистой ткани у млекопитающего, включающий введение в инфицированную область указанного млекопитающего терапевтически эффективного количества композиции по любому из пп. 4-7 в течение эффективного количества времени.9. Способ по п. 8, где терапевтически эффективное количество композиции включает пептид в концентрации в диапазоне от примерно 0,1 мкг/мл до примерно 10% (масс./об.).10. Способ по п. 8, где микробная инфекция вызвана бактерией, выбранной из группы, состоящей из P. acnes, S. aureus, Ε. coli и С.albicans.11. Способ по п. 8, где микробная инфекция кожи представляет собой акне, атопический дерматит, розацеа, бактериальный вагино1. A peptide of the formula: Slipid-lysine-proline-N; Slipid-lysine-d-proline-NH; Slipid-lysine-histidine-NH or Slipid-lysine-arginine-NH. 2. The peptide according to claim 1, wherein the Slipid is a lipid fragment of lauric acid (C12), myristic acid (C14), pentadecanoic acid (C15), palmitic acid (C16) or stearic acid (C18). 3. The peptide according to claim 1, wherein the peptide is palmitoyl-lysine-proline-NH; palmitoyl-lysine-d-proline-NH; palmitoyl-lysine-histidine-NH or lipalmitoyl-lysine-arginine-NH. 4. A composition comprising at least one peptide according to any one of paragraphs. 1-3 and a pharmaceutically acceptable carrier. 5. A composition according to claim 4, wherein the peptide is present in a concentration in the range of from about 0.1 μg / ml to about 10% (w / v). A composition according to claim 4 or 5, wherein the composition is in the form of an aerosol, cosmetic preparation, spray, emulsion, liquid, lotion, cream, paste, ointment, powder or foam. A composition according to claim 6, which can be used to prevent or treat skin conditions of acne, atopic dermatitis, rosacea, bacterial vaginosis, dandruff or epidermophytosis of the feet. A method for the prevention or treatment of a microbial infection of a skin or mucous tissue in a mammal, comprising administering to the infected area of said mammal a therapeutically effective amount of a composition according to any one of claims. 4-7 for an effective amount of time. 9. The method of claim 8, wherein the therapeutically effective amount of the composition comprises a peptide in a concentration in the range of about 0.1 μg / ml to about 10% (w / v). The method of claim 8, wherein the microbial infection is caused by a bacterium selected from the group consisting of P. acnes, S. aureus, Ε. coli and C. albicans. 11. The method of claim 8, wherein the microbial infection of the skin is acne, atopic dermatitis, rosacea, bacterial vagina

Claims (14)

1. Пептид формулы:1. The peptide of the formula: C12-18 липид-лизин-пролин-N2;C 12-18 lipid-lysine-proline-N 2 ; C12-18 липид-лизин-d-пролин-NH2;C 12-18 lipid-lysine-d-proline-NH 2 ; C12-18 липид-лизин-гистидин-NH2 илиC 12-18 lipid-lysine-histidine-NH 2 or C12-18 липид-лизин-аргинин-NH2.C 12-18 lipid-lysine-arginine-NH 2 . 2. Пептид по п. 1, где C12-18 липид является липидным фрагментом лауриновой кислоты (С12), миристиновой кислоты (С14), пентадекановой кислоты (С15), пальмитиновой кислоты (С16) или стеариновой кислоты (С18).2. The peptide according to claim 1, where the C 12-18 lipid is a lipid fragment of lauric acid (C12), myristic acid (C14), pentadecanoic acid (C15), palmitic acid (C16) or stearic acid (C18). 3. Пептид по п. 1, где пептид представляет собой3. The peptide according to claim 1, where the peptide is a пальмитоил-лизин-пролин-NH2;palmitoyl-lysine-proline-NH 2 ; пальмитоил-лизин-d-пролин-NH2;palmitoyl-lysine-d-proline-NH 2 ; пальмитоил-лизин-гистидин-NH2 илиpalmitoyl-lysine-histidine-NH 2 or пальмитоил-лизин-аргинин-NH2.palmitoyl-lysine-arginine-NH 2 . 4. Композиция, содержащая по меньшей мере один пептид по любому из пп. 1-3 и фармацевтически приемлемый носитель.4. A composition comprising at least one peptide according to any one of paragraphs. 1-3 and a pharmaceutically acceptable carrier. 5. Композиция по п. 4, где пептид присутствует в концентрации в диапазоне от примерно 0,1 мкг/мл до примерно 10% (масс./об.).5. The composition of claim 4, wherein the peptide is present in a concentration in the range of about 0.1 μg / ml to about 10% (w / v). 6. Композиция по п. 4 или 5, где композиция представлена в виде аэрозоля, косметического препарата, спрея, эмульсии, жидкости, лосьона, крема, пасты, мази, порошка или пены.6. The composition according to p. 4 or 5, where the composition is presented in the form of an aerosol, cosmetic product, spray, emulsion, liquid, lotion, cream, paste, ointment, powder or foam. 7. Композиция по п. 6, которая может быть использована для профилактики или лечения кожных состояний акне, атопического дерматита, розацеа, бактериального вагиноза, перхоти или эпидермофитии стоп.7. The composition according to p. 6, which can be used for the prevention or treatment of skin conditions of acne, atopic dermatitis, rosacea, bacterial vaginosis, dandruff or epidermophytosis of the feet. 8. Способ профилактики или лечения микробной инфекции кожи или слизистой ткани у млекопитающего, включающий введение в инфицированную область указанного млекопитающего терапевтически эффективного количества композиции по любому из пп. 4-7 в течение эффективного количества времени.8. A method of preventing or treating a microbial infection of a skin or mucous tissue of a mammal, comprising administering to the infected area of said mammal a therapeutically effective amount of a composition according to any one of claims. 4-7 for an effective amount of time. 9. Способ по п. 8, где терапевтически эффективное количество композиции включает пептид в концентрации в диапазоне от примерно 0,1 мкг/мл до примерно 10% (масс./об.).9. The method of claim 8, wherein the therapeutically effective amount of the composition comprises a peptide in a concentration in the range of about 0.1 μg / ml to about 10% (w / v). 10. Способ по п. 8, где микробная инфекция вызвана бактерией, выбранной из группы, состоящей из P. acnes, S. aureus, Ε. coli и С.albicans.10. The method of claim 8, wherein the microbial infection is caused by a bacterium selected from the group consisting of P. acnes, S. aureus, Ε. coli and C. albicans. 11. Способ по п. 8, где микробная инфекция кожи представляет собой акне, атопический дерматит, розацеа, бактериальный вагиноз, перхоть или эпидермофитию стоп.11. The method according to p. 8, where the microbial infection of the skin is acne, atopic dermatitis, rosacea, bacterial vaginosis, dandruff or epidermophytosis of the feet. 12. Применение пептида по любому из пп. 1-3 или композиции по любому из пп. 4-7 при производстве лекарственного средства для профилактики или лечения микробной инфекции кожи или слизистой ткани у млекопитающего.12. The use of the peptide according to any one of paragraphs. 1-3 or composition according to any one of paragraphs. 4-7 in the manufacture of a medicament for the prevention or treatment of a microbial infection of a skin or mucous tissue in a mammal. 13. Применение по п. 12, где микробная инфекция вызвана бактерией, выбранной из группы, состоящей из P. acnes, S. aureus, Ε. coli и С.albicans.13. The use of claim 12, wherein the microbial infection is caused by a bacterium selected from the group consisting of P. acnes, S. aureus, Ε. coli and C. albicans. 14. Применение по п. 12 или 13, где микробная инфекция кожи представляет собой акне, атопический дерматит, розацеа, бактериальный вагиноз, перхоть или эпидермофитию стоп. 14. The use according to claim 12 or 13, wherein the microbial infection of the skin is acne, atopic dermatitis, rosacea, bacterial vaginosis, dandruff or epidermophytosis of the feet.
RU2014142038A 2012-03-20 2013-03-07 Short antimicrobial lipopeptides RU2627648C2 (en)

Applications Claiming Priority (3)

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US201261613212P 2012-03-20 2012-03-20
US61/613,212 2012-03-20
PCT/US2013/029696 WO2013142088A1 (en) 2012-03-20 2013-03-07 Short antimicrobial lipopeptides

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KR (1) KR20140136494A (en)
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JP6906274B2 (en) * 2014-06-30 2021-07-21 ロート製薬株式会社 Topical compositions, ophthalmic compositions, antibacterial agents, and antibacterial methods
US10835572B2 (en) 2014-06-30 2020-11-17 Rohto Pharmaceutical Co., Ltd. Composition for external application
WO2017035345A1 (en) * 2015-08-26 2017-03-02 The General Hospital Corporation System and method for electrical control of bacteria
KR101855170B1 (en) 2015-11-18 2018-05-08 (주)노바셀테크놀로지 A novel antimicrobial peptide and use thereof
CN109320585B (en) * 2018-09-06 2021-10-26 南方医科大学 Short lipopeptide with specific anti-acne propionibacterium effect and anti-inflammatory effect
US20220257569A1 (en) * 2018-09-12 2022-08-18 The Governing Council Of The University Of Toronto Indole-oxadiazole compounds and their therapeutic use
CN111035764B (en) * 2018-10-14 2021-09-07 深圳市健元医药科技有限公司 Composition for treating rheumatoid arthritis and preparation method thereof
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